Ammonia → HCID 13851197, compound

HRID 978455Notes

Reaction equation

HRID 978455 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]4[C:32](=[O:33])[C:31]5[C:26](=[CH:27][C:28]([OH:34])=[CH:29][CH:30]=5)[NH:25][C:24]4=[O:35])[CH2:15][CH2:14]3)OCCO2)=[CH:4][CH:3]=1.Cl.N>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]3[C:32](=[O:33])[C:31]4[C:26](=[CH:27][C:28]([OH:34])=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:35])[CH2:15][CH2:14]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 20202893HCID 20202893, compound

Product 1

HCID 13851197HCID 13851197, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.9 parts of 3-[4-[4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-1-piperidinyl]butyl]-7-hydroxy-2,4(1H,3H)-quinazolinedione, 10 parts of a hydrochloric acid solution 6N and 20 parts of ethanol was stirred for 4 hours at reflux temperature. The base was liberated with ammonia. The product was filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 0.5 parts (28%) of 3-[4-[4-(4-fluorobenzyl)-1-piperidinyl]butyl]-7-hydroxy-2,4(1H,3H)-quinazolinedione; mp. 207.9° C. (27).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe product was filtered off
  3. custompurified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-ba0b481a2b9a4fe689cb81c833335ce5
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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